(2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Base Information

• Chemical Name: (2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate
• CAS No.: 52141-84-1
• Molecular Formula: C₂₉H₂₈N₂O₅S
• Molecular Weight: 516.618
• Mol file: 52141-84-1.mol

Synonyms:(2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Chemical Property of (2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

There total 3 articles about (2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.8%

1,1-Diphenylmethanol (91-01-0) + penicilin V (87-08-1) → (2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate (52141-84-1)

Guidance literature:

With pyridine; isocyanuric acid; In dichloromethane; at -7 - -5 ℃; for 0.666667h;

DOI:10.3987/COM-90-5565

Reference yield: 63.0%

O-diphenylmethyl 2,2,2-trichloroacetimidate (100865-93-8) + penicilin V (87-08-1) → (2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate (52141-84-1)

Guidance literature:

In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1055/s-0033-1340293

Reference yield:

1,1-Diphenylmethanol (91-01-0) → (2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate (52141-84-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / Inert atmosphere

2: dichloromethane / 18 h / 20 °C / Inert atmosphere

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1055/s-0033-1340293

upstream raw materials:

1,1-Diphenylmethanol

penicilin V

O-diphenylmethyl 2,2,2-trichloroacetimidate

Downstream raw materials:

benzhydryl (2R,4S)-2-<(1R)-2-acetoxy-1-phenoxyacetylaminoethyl>-5,5-dimethylthiazolidine-4-carboxylate

benzhydryl (2R,4S)-2-<(1R)-2-hydroxy-1-phenoxyacetylaminoethyl>-5,5-dimethylthiazolidine-4-carboxylate

(R)-3-Methyl-2-[(S)-2-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-butyric acid benzhydryl ester

(2S,5R,6R)-6-[tert-Butoxycarbonyl-(2-phenoxy-acetyl)-amino]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester